2040’s Ideas and Innovations Newsletter, Issue 25: How to Manage a Five Generation Workforce

Kevin Novak
12 min readOct 14, 2021


Managing a Five Generation Workforce in 2021 and Beyond

Our Lack of Context Leads to Over-Generalizations

We are at an interesting inflection point: Five different generations make up today’s workforce: Gen Z, millennials, Gen X, boomers and the Silent Generation. And the Alphas are not far behind. Add to the age differences, the new rules of diversity and inclusion, changes in life stage definitions, individual and group values, and the impact of evolving societal events. For starters, 2020 Pew Research reveals 59% of Gen Zers say forms or online profiles should include additional gender options, compared with 50% of millennials, 40% of Gen Xers, 37% of boomers and 32% in the Silent Generation.

Each generation approaches their careers differently and each needs to be managed in nuanced ways. Older workers value a slow, steady and consistent career path, but according to trends expert Jasmine Glasheen, “Next gens are more focused on helping the collective whole through self-realization — which translates into pursuing a career path that’s centered around individual evolution/success.”

Most importantly, all generations are inseparable from technology. That being said next gens are more comfortable with data. Younger decision-makers are terrific champions for the transition to data-driven business culture. Younger generations are more willing to embrace change; 76% of executives in their 30s or younger look for opportunities to leverage new technology to achieve business goals. Plus, 67% of them see risk as opportunity, not danger, according to an Inavero study.

A World of Differences

Our planet has nearly 8 billion individuals. This is an incredible number that is often hard to grasp, let alone understand and relate to. How can we expand our sensitivity to so many different types of people from so many different backgrounds and cultures when our minds are limited to what we have only seen and experienced personally? Our understanding is largely formed by our own mental constructs.

As a result, we seek to conceptually classify and categorize the groups that comprise these 8 billion people. As the human world grows and continues to dynamically change, our default to oversimplification leads to faulty conclusions and misinterpretations. We frequently overgeneralize how we define “the herds” and miss important influences, nuances, variables, and factors of the individuals in these groups.

As we discuss the very real nuances describing generations and the intergenerational issues that form a workforce in today’s society, we must recognize we are the sum of our parts. Regardless of where we fall in the age bands of any generation, we are further defined by our life stages (single, married, divorced, parent, single-parent, recent graduate, early-career professional, late-career professional, etc.) our belief systems, and how we are touched by societal events (terrorism, political unrest, war, economic collapse … and yes even a pandemic).

Some would represent that we are all individually unique. Our ability to capture and interpret data shows that we are all not as unique as we would like to believe. Humans are complex and the result of a variety of influences. The capture of a few individual bits of data here or there based on our actions allow us to be herded into groups and segmented by behaviors, values, preferences, and the like.

The Five Generations

Let’s look at the five generations that make up our workforce today.

The Silent Generation is the oldest employee group born between 1925–1945 and comprises only 2% of today’s workforce. They are also called the Traditionalists, a generation of workers that values traditional benefits.

Baby Boomers were born between 1946 and 1964 and make up 25% of the workforce. Kiely Kuligowski of business.com says, “The Vietnam War, the first Civil Rights Movement and Watergate were the major world events that helped shape the baby boomer generation. Many boomers do not have enough money saved for a comfortable retirement and may work into their 70s. When working with boomers, provide clear, specific goals and deadlines, offer them mentoring opportunities where they can share their experience, and place them in team settings.” In terms of work characteristics, she adds, boomers are generally known for:

  • Job loyalty
  • Self-motivation
  • High work ethic
  • Being competitive
  • Willing to make personal sacrifices for professional success

Generation X workers, born between 1965 and 1980 comprise nearly 33% of the workforce. According to Amwins, Generation X values work-life balance, such as flexible working hours, childcare and financial protection, as they tend to carry the most dependents and oftentimes are caretakers to their boomer parents. PricewaterhouseCoopers reports more than 53% of Gen X employees are worried about their financial well-being, as many are burdened with settling extensive student loans and paying for their children’s education. This generation knows what they want and has the resources and skills to find what they need. Kuligowski states, “The major world events that shaped Gen X include the AIDS epidemic, the fall of the Berlin Wall, the invention of the internet and the subsequent dot-com boom. In managing Gen X employees, aim to be efficient, provide direct feedback, and offer them plenty of independence.” She says Gen Xers are known for being:

  • Efficient
  • Direct in their communication style
  • Adaptable to new technologies
  • Independent
  • Steady and dependable

Millennials born between 1981 and 1996 is the fastest-growing segment of the workforce and the largest at 35%. According to Harvard Pilgrim, by 2025 millennials will take over a much larger market share and comprise 74% of the workforce. And according to Amwins, “Like Gen Xers, a primary concern for millennials is managing debt, as they have accrued an unprecedented amount of student loan debt. Millennials have adopted an ‘anything can happen’ mentality and are willing to pay for peace of mind to be financially stable. Other desirable benefits for millennials include student loan repayment benefits and flexible work hours. While millennials are known to frequently switch jobs, up to 34% do so because their positions lack work flexibility. Kuligowski adds, “The major world events that defined the millennial generation include the Columbine shooting, 9/11 and the advent of the internet. Millennials started their careers during a recession in the 90s which has impacted how they view long-term careers. They care about their performance and are confident in judging their managers. When working with millennials, get to know them personally, communicate in-depth with them about their progress and output, and offer flexible work schedules.” You also need to be transparent and honest with them. “More importantly, never judge their work by the hours they put in, but with their results. Millennials demand a work-life balance above everything else. Millennials assert themselves and question the status quo — suggesting a change to a policy that seems inefficient, for example — can also cause undue trouble,” adds Dr. Jeffrey Arnett, Developmental Psychologist. Kuligowski adds millennial employees are:

  • Competitive
  • Achievement-oriented
  • Tech-savvy
  • Focused on work-life balance
  • Open to seeking out unique work experiences

Gen Z was born between 1997 and 2012 and are the first true tech natives, born into a world with an evolved internet. Gen Z is known for being the most diverse generation in American history. Generation Z employees are especially concerned about job security, and they place value on benefits that support career growth and development. Additionally, Amwins says,” Gen Zers are more likely to weigh supplemental benefits as part of total compensation, seeking out offerings like flexible paid time off (PTO), tuition reimbursement, pet insurance and accident insurance. Prior to the COVID-19 pandemic, this generation did not appreciate the full range of employee benefits but now are placing more importance on benefits that support their overall wellbeing like mental-health benefits and Employee Assistance Programs (EAPs).” Kuligowski adds, “Major world events that defined Gen Z include exposure to violent events (Sandy Hook, the Boston Marathon bombing, worldwide terrorism), significant technological advancements, the Great Recession and a global pandemic. When working with Gen Z, give them opportunities to multitask, provide lots of autonomy and self-direction and offer a solid work-life balance.” She says Gen Z’s major characteristics are:

  • Diverse
  • Open-minded, progressive
  • Tech-savvy
  • Individualist and creative
  • Self-directed


As humans, we are controlled consciously and unconsciously by our personal biases. And according to Professor Megan Gerhardt, director of leadership development at Miami University’s Farmer School of Business and author of Gentelligence, “What we value as individuals is often influenced by events completely out of our control, dictated by our experiences at the beginnings of our lives and our careers. Each generation enters the workforce under certain conditions, which ultimately helped to shape our sense of purpose, our preferences, and our drivers for success.”

You can’t manage what you don’t understand. Gerhardt adds, “Many of the generational conversations in the news today rely on false stereotypes and clickbait headlines, rather than taking the time to understand the important differences that are a part of our generational identities. When we assign negative or overarching characteristics to each group, we imply that their values, beliefs, and goals are fundamentally flawed.” She advises challenging these harmful stereotypes:

  • The Silent Generation: loyal but traditional
  • Boomers: collaborative but averse to change
  • Generation X: independent but bleak
  • Millennials: driven but entitled
  • Generation Z: progressive but disloyal

Millennials take on the brunt of stereotypical profiling. They are typically viewed as entitled, lazy, and narcissistic. Arnett says, “What is true is that they have high expectations of work; they expect it to be more than just bringing home a paycheck. They are looking for identity-based work, something they enjoy that suits their abilities and interests. The problem is many profit-driven workplaces aren’t designed to offer that type of self-fulfillment. Plus, some employers and older colleagues find that search for more meaningful work exasperating, viewing it as having a sense of entitlement. That’s partly where the stereotypes come from. The fact that they are willing to question and offer criticism is something that can make an organization better. If you dismiss that, they will look for something else, and probably find it.”


“Each generation has different values it prizes. For example, Gen X appreciates flexible working arrangements and promotional opportunities; boomers value individuality and material success; millennials like personal freedom and engaged workplaces; and Gen Zers prioritize creativity and progressive thinking. It can be challenging to meet everyone’s differing values and provide them with a workplace that supports them,” states Kuligowski.

Glasheen adds, “Next gens refuse to work the entry-level jobs for which their parents were grateful. Paying your dues isn’t part of their reality. Instead, they see being stuck in a career they don’t enjoy as being oppressed by the one percent. This makes it challenging for employers to fill entry-level positions and retain younger employees. Boomer and Silent Generation employers can no longer treat entry-level employees like they were treated in the early days of their own careers. The dissonance comes when employers expect the next gens to do grunt work, give away their ideas without recognition, and work in “thankless” jobs for the long term. Retail employers that want next gens to invest in a career their companies need to provide accelerated advancement opportunities, as well as authentic recognition and praise. Deloitte found that 49 percent of millennials said they would quit their current job in the next two years if given the choice. “Pay/financial rewards” were the main incentive for the intended turnover (43 percent). However, “lack of opportunities to advance (35 percent),” “lack of learning and development opportunities (28 percent),” “not feeling appreciated (23 percent),” “work-life balance (22 percent),” “boredom (21 percent)” and “culture (15 percent)” also played a role for some.

Managing a Multigenerational Workforce

Look for innovation and actionable solutions resulting from cross-generational, cross-function teams. Keep everyone connected and ensure they feel included. Be mindful of the need for clarity. Operate with purpose and enable employees to see there’s a place for each of them. Provide meaningful work and professional growth. And be trustworthy; show employees that you care for their welfare. Create the kind of environment in which every person feels willing to ask for help, share their best ideas, and take risks. Gerhardt says you need to prioritize psychological safety. “People come to conversations with different experiences and varying levels of willingness to engage. The role of the manager is to provide ongoing opportunities to have discussions — not to force people to a particular point of view or to check a box.”

“A multigenerational workforce provides opportunities for learning and innovation,” states Kuligowski. “Employees of different ages offer plenty of opportunities to share experiences, ideas and thoughts with each other. Combining multiple generations is a great way to effectively problem-solve and come up with creative solutions to challenges your company is facing. Each generational cohort has its unique characteristics, values, and outlooks, and familiarizing yourself with each generation can help you create a collaborative, productive workplace. Employees are unique, and you should treat your employees as individuals first and foremost.

  1. Be flexible. The most important thing you can do with a multigenerational workforce is to be flexible, with everything from working hours to communication styles. Creating a culture of flexibility inspires your employees to be flexible as well, which can help resolve disagreements or differing thoughts on how things are done.
  2. Understand your employees. Get to know your employees, not just their generational characteristics, but as individuals. “My best advice for managing a multigenerational workforce is to listen and understand how your teams do their best work,” says Miles Beckler, founder and entrepreneur at MilesBecker.com. “Certain workers are very visual, while others are auditory or even social. Assigning people tasks that harmonize with their personal style or putting them in teams that complement their skill sets, are important strategies for improving productivity.”
  3. Provide opportunities for employees to learn from each other. Each age group has a wealth of knowledge and experience — it’s in your best interests to create channels where that knowledge can be shared, e.g., a mentorship program where baby boomers are paired with millennials or Gen Zers, or a mutual mentorship where members of two different generations work together as a team. This can promote team bonding, help your team members understand each other and create higher employee engagement.
  4. Avoid stereotypes. Muhammad Shabbar, HR and admin manager at AI Manal Development, advises business owners and managers to “avoid generational conflict by removing stereotypes. Regardless of generation, work harmony can be achieved if these assumptions are removed.”
  5. Tailor your communication methods. Since each generation tends to have its favored methods of communication (in person for boomers, email for Gen X, mobile for Z), communicate with each of your team members according to their preferences. It may not seem like much, but it demonstrates your recognition of their preferences and that you value them.

Portfolio Careers

Switching jobs is no longer a sign of instability or failure. Glasheen says,” The average modern worker holds around 12.5 different jobs in their lifetime. The younger a worker, the more probable it is that they’ll leave their current job for a better opportunity — sooner than later. A recent study by The Balance Careers found that the median job tenure among workers ages 25 to 34 is just 2.8 years. The median job tenure for ages 35 to 44, on the other hand, is 4.9 years. That number jumps to 7.6 years for workers ages 45 to 54, and an impressive 10.1 years for workers ages 55 to 64. The next-gen paradigm is, “if the shoe fits, maybe another shoe would fit better.”

An updated way to look at next-gen job fluidity is to think of portfolio careers. April Rinne, author Flux: 8 Superpowers for Thriving in Constant Change, has been a proponent of portfolio careers. According to Rinne, “A portfolioist takes inspiration from other disciplines to create an adaptable, diversified, and personal career. This portfolio of skills, experience, roles or responsibilities might be wildly diverse, which both distributes risk and allows for experimentation. The portfolioist’s career is a bento box, with each skill in its place.” The concept is you take your portfolio with you and apply it to a series of career moves. She adds, “It’s about creating your own platform and honing valuable skills. In short, it’s about curating a portfolio of work that reflects you and maximizes your potential in the world. what is new about the way portfolioism can be manifest today is the degree to which individuals have agency over the portfolios that they build. The most important baseline criterion for becoming a portfolioist is open-mindedness. Most successful portfolioists have a blend of short-, medium- and long-term engagements, with different pay levels and working arrangements.”

How does that play into an organizational culture? Younger employees will thrive by moving around in the organization and honing their portfolio of skills that they can apply to a range of business challenges.

A Path Forward

Today’s workforce spans generations, social strata, race, and gender. However, according to Deloitte, only six percent of survey respondents “strongly agree” that their leaders are prepared to effectively lead a multigenerational team. At 2040 we help our clients understand that Gen X, Boomers and Silents leaders need to realize that they can’t treat next-gen workers and cohorts in the same way that their first employers treated them. By implementing worker segmentation, organizations can create career paths for their workers instead of just jobs — creating a business that evolves with its employees — which is the key to long-term employee retention across the generational divide.

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Kevin Novak

4X webby winner, CEO and Chief Strategy Officer @2040 Digital (www.2040digital.com), IADAS Member, Speaker, Author, Science Nut